Methanesulfonyl chloride → HCID 53691273, compound

Participants

Reaction Steps

95 g (0.258 mole) of 5α,6β-dihydroxy-17-bromo-androsta-2,16-diene obtained as described in section (b) of Example 2 are reacted with 21 ml (0.276 mole) of methanesulfonic acid chloride, as described in section (c) of Example 2, but with the difference that the mixture of products obtained after evaporation of the dichloro methane extract is dissolved in 16-fold amount (calculated on the starting material) of ethanol and the 12% aqueous solution of 19 g of sodium hydroxide is added to the ethanolic solution. The reaction mixture is heated to reflux for 10 minutes, then cooled to room temperature and the pH value is adjusted to 7 with acetic acid. The solvent is then distilled off, the evaporation residue is triturated with water. The precipitated product is filtered off, washed with water until the washings are neutral and dried over phosphorous pentoxide in vacuo. The obtained product is recrystallized from acetonitrile. Yield: 89% of 5α,6α-epoxy-17-bromo-androsta-2,16-diene; m.p. 146°-147° C; [α]D25 = - 18.3° (c = 1 in chloroform).

Provenance & Evidence